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First examples of the reactions of 3-trimethylsilyl-2-propynamides with organic diselenides yielding 3-alkylselanyl-2-propenamides and 3-organylselanyl-2-propynamides were realized. The latter compounds were obtained by the Cu-catalyzed reaction of organic diselenides with 4-propioloylmorpholine. The reaction of 3-trimethylsilyl-2-propynamides with dialkyl diselenides in the system NaBH4/H2O/K2CO3/THF proceeded in a regio- and stereoselective fashion, affording 3-alkylselanyl-2-propenamides in 90–94% yields. An unsymmetrical divinyl selenide with the cyclic amide groups and a product, containing two selanyl-2-propenamide moieties and three cyclic amide groups, were synthesized. The Cu-catalyzed allylation reaction of 3-trimethylsilyl-2-propynamides was accompanied with desilylation to yield 3-allyl-2-propynamides. [ABSTRACT FROM AUTHOR]

An efficient approach to a novel family of (Z)-3-amino-3-oxo-1-propenyl selenocyanates was developed based on the reaction of KSeCN with 3-trimethylsilyl-2-propynamides in the presence of ammonium chloride in methanol. The reaction was accompanied by a desilylation process. The products were not formed under the same reaction conditions in the absence of ammonium chloride, which was used for the first time in the reactions of selenocyanates with acetylenes. The use of this new methodology allowed the reaction to carry out in a regio- and stereoselective fashion as anti-addition affording vinyl selenocyanates with a (Z)-configuration in high yields. [ABSTRACT FROM AUTHOR]